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Attending the premiere of The Banshees Of Inisherin | New York City, NY | October 10, 2022

Stella McCartney ‘Single Breasted Oversize Blazer’ – $1,495.00

Taylor is really gravitating towards boxier/oversized silhouettes these days. With a pair of wide leg pants like these, I think either committing to an intentionally oversized/baggy look is very on trend as of late.

My personal preference would be to offset a wide leg trouser like this with a more tailored blazer – but I’m also not one to look a gift blazer in the mouth.

Worn with: Etro bag and Prada loafers

Get the look: Aqua, $70.80

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Midnights Mayhem with Me (x) | September 21, 2022

Smythe ‘90s Blazer’ – $695.00

I’ve recently made it a personal goal for myself to develop an enviable blazer collection and let me tell you, the warm brown fall girl colour and perfectly just oversized silhouette of this one by Smythe is doing something to me.

I also love the way the colour of this blazer (and the corresponding crushed velvet curtains behind her) ties in with the palette and aesthetic served to us thus far.

Get the look: ASOS, $53.00

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Out and about | Beverly Hills, CA | June 29, 2022

Stella McCartney ‘Cat Print Hoodie’ – $550.00 (sold out)

*Taylor very clearly did not want to be seen in these images. In keeping with TSS identification principles, I’ve cropped her face to retain focus on the clothes for those interested in such details.

I suspect Taylor’s love of Stella’s clothes will stick around for quite some time if the designer keeps putting cats on things.

Worn with: Ralph Lauren bag and Juju sandals

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Benjamin is 22 in cat years. | December 27, 2021

Stella McCartney ‘The Beatles Get Back Tie Dye Hoodie’ – $895.00

A double English moment! Just as Taylor collaborated with British designer Stella McCartney to create an exclusive line of merch for her album Lover, Stella also created a line of Beatles merch in – dare I say – Lover-esque colours. Given Stella’s obvious connection to both Taylor and The Beatles, this is a really sweet moment.

Get the look: Topman, $56.00

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Saturday Night Live after-party | New York City, NY | November 13, 2021

Anine Bing ‘Kaia Double-Breasted Blazer’ – $400.00

To head to the SNL after-party with the likes of Sadie Sink and Blake Lively, it appears Taylor threw on this enviable houndstooth blazer over her “All Too Well” (10 Minute Version) performance bodysuit.

I, for one, would wear this entire outfit in a heartbeat.

Worn with: Silk slip mask, Jennifer Zeuner earrings, Vince Camuto bag, and Aquazzura boots

Get the look: Missguided, $42.00

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Saturday Night Live | November 13, 2021

Area ‘Cropped Crystal Embellished Wool Blend Blazer’ – $1,580.00
Area ‘Crystal Slit Trousers’ – $1,150.00

I absolutely love that at first glance this appears to be a polished business-like plaid suit set. But upon second glance there’s crystal embellishments, a cropped midriff, and … oh, yeah. Slits in the ass. For a literal cheeky moment. I’m obsessed.

Worn with: Mindi Mond earrings